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Former One Direction<\/a> heartthrob Harry Styles<\/strong><\/a> has had his fair share of romantic relationships since becoming a global icon in 2010. The ex-boy-bander surprised fans when he was spotted getting cozy<\/a> with ex-girlfriend Olivia Wilde <\/strong><\/a>in January 2021 \u2013 who directed him in the film Don\u2019t Worry Darling\u00a0<\/em>\u2014 before their split nearly two years later.<\/p>\n The former couple was first photographed holding hands while attending Harry\u2019s manager Jeff Azoff<\/strong>\u2018s wedding in Montecito, California, in January 2021, while the movie was still shooting in Los Angeles. The shocking snapshots came two months after the Tron: Legacy<\/em> star and her ex-fianc\u00e9, Jason Sudeikis<\/strong><\/a>, called off their engagement<\/a>.<\/p>\n \u201cThe pair held hands and looked very much like a loved-up couple,\u201d an insider exclusively told Life & Style<\/em> of Harry and Olivia at his friend\u2019s wedding. \u201cThey seemed very comfortable with each other \u2014 almost like they\u2019ve been dating for months, not just weeks.\u201d<\/p>\n hough their relationship was seemingly moving in the right direction, Harry and Olivia parted ways in November 2022.<\/p>\n Prior to his relationship with Olivia, Harry dated Victoria\u2019s Secret<\/a> model Camille Rowe<\/strong><\/a>. The pair sparked romance rumors in June 2017, when they were spotted at a Fleetwood Mac concert in New York together. The former face of Chloe followed the singer around the globe during his 2017-2018 world tour for his self-titled debut album, but they split in June 2018.<\/p>\n The breakup deeply affected the 1D alum, who went on to write his second album, Fine Line<\/em>, which was heavily inspired by their relationship. Harry even went as far as to include a recording of the Playboy<\/em><\/a> cover girl\u2019s voice on his song, \u201cCherry,\u201d<\/a> one of the sadder songs on the record.<\/p>\n \u201cWhen we listened back to the album, I asked her to add it in,\u201d he told Rolling Stone<\/em><\/a> in August 2019. \u201cI wanted [\u201cCherry\u201d] to reflect how I felt then. I was feeling not great. It\u2019s all about being not great. Because you get petty when things don\u2019t go the way you want it. There\u2019s parts that [are] so pathetic.\u201d<\/p>\n Camille isn\u2019t the only woman the U.K. native has written music about. Harry has been linked to Kendall Jenner<\/a>\u00a0<\/strong>many times over the years \u2014 especially in January 2016, when the former flames were photographed cuddling and kissing on a yacht in St. Barts. In December 2019, the exes appeared on The Late Late<\/em> Show<\/em> together when Harry filled in for host James Corden<\/strong> \u2014 and the 818 Tequila founder asked Harry which songs on his debut album were written about her<\/a>.<\/p>\n However, she posed the question during the infamous game Spill Your Guts or Fill Your Guts<\/a>, so the Dunkirk<\/em> star opted to eat cod sperm (yes, you read that right) instead of revealing any titles.<\/p>\n